Acetone

Acetone

Names
Preferred IUPAC name Propan-2-one
Other names Acetone Dimethyl ketone Dimethyl carbonyl β-Ketopropane Propanone 2-Propanone Dimethyl formaldehyde Pyroacetic spirit (archaic) Ketone propane
Identifiers
CAS Number	67-64-1 Y
3D model (Jmol)	Interactive image
3DMet	B00058
Abbreviations	DMK
Beilstein Reference	635680
ChEBI	CHEBI:15347 Y
ChEMBL	ChEMBL14253 Y
ChemSpider	175 Y
ECHA InfoCard	100.000.602
EC Number	200-662-2
Gmelin Reference	1466
KEGG	D02311 Y
MeSH	Acetone
PubChem	180
RTECS number	AL3150000
UNII	1364PS73AF Y
UN number	1090
InChI InChI=1S/C3H6O/c1-3(2)4/h1-2H3 Y Key: CSCPPACGZOOCGX-UHFFFAOYSA-N Y InChI=1/C3H6O/c1-3(2)4/h1-2H3 Key: CSCPPACGZOOCGX-UHFFFAOYAF
SMILES CC(=O)C
Properties
Chemical formula	C3H6O
Molar mass	58.08 g·mol−1
Appearance	colorless liquid
Odor	pungent, irritating, floral
Density	0.7845 g cm−3 (25 °C)
Melting point	−94.7 °C (−138.5 °F; 178.5 K)
Boiling point	56.05 °C (132.89 °F; 329.20 K)
Solubility in water	miscible
Solubility	miscible in benzene, diethyl ether, methanol, chloroform, ethanol
log P	−0.042
Vapor pressure	9.39 kPa (0 °C) 30.6 kPa (25 °C) 374 kPa (100 °C) 2.8 MPa (200 °C)
Acidity (pKa)	19.2
Basicity (pKb)	−5.2 (for conjugate base)
Magnetic susceptibility (χ)	-33.78·10−6 cm3/mol
Refractive index (nD)	1.3588 (VD=54.46)
Viscosity	0.295 mPa·s (25 °C)
Structure
Coordination geometry	Trigonal planar at C2
Molecular shape	Dihedral at C2
Dipole moment	2.91 D
Thermochemistry
Specific heat capacity (C)	125.45 J/mol·K
Std molar entropy (So298)	200.4 J/mol·K
Std enthalpy of formation (ΔfHo298)	−250.03-(−248.77) kJ/mol
Std enthalpy of combustion (ΔcHo298)	−1.772 MJ/mol
Hazards
Safety data sheet	See: data page
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H225, H319, H336
GHS precautionary statements	P210, P261, P305+351+338
EU classification (DSD)	F Xi
R-phrases	R11, R36, R66, R67
S-phrases	(S2), S9, S16, S26
NFPA 704	3 1 0
Flash point	−20 °C (−4 °F; 253 K)
Autoignition temperature	465 °C (869 °F; 738 K)
Explosive limits	2.6–12.8%
Threshold limit value	1185 mg/m3 (TWA), 2375 mg/m3 (STEL)
Lethal dose or concentration (LD, LC):
LD50 (median dose)	5800 mg/kg (rat, oral) 3000 mg/kg (mouse, oral) 5340 mg/kg (rabbit, oral)
LC50 (median concentration)	20,702 ppm (rat, 8 hr)
LCLo (lowest published)	45,455 ppm (mouse, 1 hr)
US health exposure limits (NIOSH):
PEL (Permissible)	1000 ppm (2400 mg/m3)
REL (Recommended)	TWA 250 ppm (590 mg/m3)
IDLH (Immediate danger)	2500 ppm
Related compounds
Related compounds	Butanone Isopropanol Urea Carbonic acid Carbonyl fluoride
Supplementary data page
Structure and properties	Refractive index (n), Dielectric constant (εr), etc.
Thermodynamic data	Phase behaviour solid–liquid–gas
Spectral data	UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Acetone (systematically named 2-propanone) is the organic compound with the formula (CH₃)₂CO. It is a colorless, volatile, flammable liquid, and is the simplest ketone.

Acetone is miscible with water and serves as an important solvent in its own right, typically for cleaning purposes in the laboratory. About 6.7 million tonnes were produced worldwide in 2010, mainly for use as a solvent and production of methyl methacrylate and bisphenol A. It is a common building block in organic chemistry. Familiar household uses of acetone are as the active ingredient in nail polish remover and as paint thinner.

Acetone is produced and disposed of in the human body through normal metabolic processes. It is normally present in blood and urine. People with diabetes produce it in larger amounts. Reproductive toxicity tests show that it has low potential to cause reproductive problems. Pregnant women, nursing mothers and children have higher levels of acetone.Ketogenic diets that increase acetone in the body are used to counter epileptic attacks in infants and children who suffer from recalcitrant refractory epilepsy.

Acetone was first produced by alchemists during the late Middle Ages via the dry distillation of metal acetates (e.g., lead acetate, which produced "spirit of Saturn" (since the alchemical symbol for lead was also the astrological symbol for the planet Saturn)).

In 1832, French chemist Jean Baptiste Dumas and German chemist Justus von Liebig determined the empirical formula for acetone. In 1833, the French chemist Antoine Bussy named acetone by adding the suffix -one to the stem of the corresponding acid (viz, acetic acid). By 1852, English chemist Alexander William Williamson realized that acetone was methyl acetyl; the following year, the French chemist Charles Frédéric Gerhardt concurred. In 1865, the German chemist August Kekulé published the modern structural formula for acetone.